Ethylene Glycol → 2-Bromo-4-(1,3-dioxolan-2-yl)thiazole

HRID 51101Notes

Reaction equation

HRID 51101 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]=[O:8])[N:6]=1.[CH2:9](O)[CH2:10][OH:11]>C1(C)C=CC=CC=1>[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)[N:6]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 177504332-Bromo-1,3-thiazole-4-carboxaldehyde

Product 1

HCID 219522862-Bromo-4-(1,3-dioxolan-2-yl)thiazoleYield 74.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Bromothiazole-4-carbaldehyde (6.56 g, 34.17 mmol) [A. T. Ung, S. G. Pyne/Tetrahedron: Asymmetry 9 (1998) 1395-1407]and ethylene glycol (5.72 ml, 102.5 mmol) were heated under reflux in toluene (50 ml),with a Dean and Stark trap fitted, for 18 hr. The product was concentrated and purified by column chromatography (15% ethyl acetate/hexane) to give the product as a yellow solid (6.03 g); m/z 236,238.

Workup

  1. customa Dean and Stark trap fitted, for 18 hr
  2. concentrationThe product was concentrated
  3. custompurified by column chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b434fdf1041b430185abc5032033adb8
Source dataset
uspto-grants-2004_03
Patent number
US06713485B2

Reaction notes

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